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| C=18 | H=26 | N=4 | O=2
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The analogue with a 1-butyl substitution on the indazole ring rather than 1-benzyl has also been sold as a designer drug under the name ADB-BINACA, but is now more commonly referred to as '''ADB-BUTINACA''' to avoid confusion with the benzyl compound.<ref>{{cite journal | vauthors = Kavanagh P, Pechnikov A, Nikolaev I, Dowling G, Kolosova M, Grigoryev A | title = Detection of ADB-BUTINACA Metabolites in Human Urine, Blood, Kidney and Liver | journal = Journal of Analytical Toxicology | date = August 2021 | pmid = 34341821 | doi = 10.1093/jat/bkab088 }}</ref><ref>{{cite journal | vauthors = Sia CH, Wang Z, Goh EM, Tan YL, Fong CY, Moy HY, Chan EC | title = Urinary Metabolite Biomarkers for the Detection of Synthetic Cannabinoid ADB-BUTINACA Abuse | journal = Clinical Chemistry | volume = 67 | issue = 11 | pages = 1534–1544 | date = November 2021 | pmid = 34387654 | doi = 10.1093/clinchem/hvab134 }}</ref><ref>{{cite journal | vauthors = Kronstrand R, Norman C, Vikingsson S, Biemans A, Valencia Crespo B, Edwards D, Fletcher D, Gilbert N, Persson M, Reid R, Semenova O, Al Teneiji F, Wu X, Dahlén J, NicDaéid N, Tarbah F, Sutcliffe OB, McKenzie C, Gréen H | display-authors = 6 | title = The metabolism of the synthetic cannabinoids ADB-BUTINACA and ADB-4en-PINACA and their detection in forensic toxicology casework and infused papers seized in prisons | journal = Drug Testing and Analysis | date = November 2021 | pmid = 34811926 | doi = 10.1002/dta.3203 | s2cid = 244490343 }}</ref><ref>{{Cite journal| doi = 10.1007/s11419-022-00615-z| issn = 1860-8973| last1 = Wang| first1 = Yue| last2 = Pan| first2 = Yefei| last3 = Yang| first3 = Hongkun| last4 = Liu| first4 = Jinlei| last5 = Wurita| first5 = Amin| last6 = Hasegawa| first6 = Koutaro| title = Quantification of MDMB-4en-PINACA and ADB-BUTINACA in human hair by gas chromatography–tandem mass spectrometry| journal = Forensic Toxicology| date = 2022}}</ref> It is a similarly potent CB<sub>1</sub> agonist, with an EC<sub>50</sub> of 6.36 nM.<ref>{{cite journal | vauthors = Cannaert A, Sparkes E, Pike E, Luo JL, Fang A, Kevin RC, Ellison R, Gerona R, Banister SD, Stove CP | display-authors = 6 | title = Synthesis and ''in Vitro'' Cannabinoid Receptor 1 Activity of Recently Detected Synthetic Cannabinoids 4F-MDMB-BICA, 5F-MPP-PICA, MMB-4en-PICA, CUMYL-CBMICA, ADB-BINACA, APP-BINACA, 4F-MDMB-BINACA, MDMB-4en-PINACA, A-CHMINACA, 5F-AB-P7AICA, 5F-MDMB-P7AICA, and 5F-AP7AICA | journal = ACS Chemical Neuroscience | volume = 11 | issue = 24 | pages = 4434–4446 | date = December 2020 | pmid = 33253529 | doi = 10.1021/acschemneuro.0c00644 | s2cid = 227246346 }}</ref><ref>{{cite journal | vauthors = Pike E, Grafinger KE, Cannaert A, Ametovski A, Luo JL, Sparkes E, Cairns EA, Ellison R, Gerona R, Stove CP, Auwärter V, Banister SD | display-authors = 6 | title = Systematic evaluation of a panel of 30 synthetic cannabinoid receptor agonists structurally related to MMB-4en-PICA, MDMB-4en-PINACA, ADB-4en-PINACA, and MMB-4CN-BUTINACA using a combination of binding and different CB<sub>1</sub> receptor activation assays: Part I-Synthesis, analytical characterization, and binding affinity for human CB<sub>1</sub> receptors | journal = Drug Testing and Analysis | volume = 13 | issue = 7 | pages = 1383–1401 | date = July 2021 | pmid = 33787091 | doi = 10.1002/dta.3037 }}</ref>
The analogue with a 1-butyl substitution on the indazole ring rather than 1-benzyl has also been sold as a designer drug under the name ADB-BINACA, but is now more commonly referred to as '''ADB-BUTINACA''' to avoid confusion with the benzyl compound.<ref>{{cite journal | vauthors = Kavanagh P, Pechnikov A, Nikolaev I, Dowling G, Kolosova M, Grigoryev A | title = Detection of ADB-BUTINACA Metabolites in Human Urine, Blood, Kidney and Liver | journal = Journal of Analytical Toxicology | date = August 2021 | pmid = 34341821 | doi = 10.1093/jat/bkab088 }}</ref><ref>{{cite journal | vauthors = Sia CH, Wang Z, Goh EM, Tan YL, Fong CY, Moy HY, Chan EC | title = Urinary Metabolite Biomarkers for the Detection of Synthetic Cannabinoid ADB-BUTINACA Abuse | journal = Clinical Chemistry | volume = 67 | issue = 11 | pages = 1534–1544 | date = November 2021 | pmid = 34387654 | doi = 10.1093/clinchem/hvab134 }}</ref><ref>{{cite journal | vauthors = Kronstrand R, Norman C, Vikingsson S, Biemans A, Valencia Crespo B, Edwards D, Fletcher D, Gilbert N, Persson M, Reid R, Semenova O, Al Teneiji F, Wu X, Dahlén J, NicDaéid N, Tarbah F, Sutcliffe OB, McKenzie C, Gréen H | display-authors = 6 | title = The metabolism of the synthetic cannabinoids ADB-BUTINACA and ADB-4en-PINACA and their detection in forensic toxicology casework and infused papers seized in prisons | journal = Drug Testing and Analysis | date = November 2021 | pmid = 34811926 | doi = 10.1002/dta.3203 | s2cid = 244490343 }}</ref><ref>{{Cite journal| doi = 10.1007/s11419-022-00615-z| issn = 1860-8973| last1 = Wang| first1 = Yue| last2 = Pan| first2 = Yefei| last3 = Yang| first3 = Hongkun| last4 = Liu| first4 = Jinlei| last5 = Wurita| first5 = Amin| last6 = Hasegawa| first6 = Koutaro| title = Quantification of MDMB-4en-PINACA and ADB-BUTINACA in human hair by gas chromatography–tandem mass spectrometry| journal = Forensic Toxicology| date = 2022}}</ref><ref>{{cite journal|first1=A.|last1=King|first2=S. L.|last2=Hill|first3=M.|last3=Pucci|first4=G.|last4=Bailey|title=Clinical features associated with ADB-BUTINACA exposure in patients attending emergency departments in England|journal=Clinical Toxicology|date=August 2022|issn=1556-3650|pages=1–5|pmid=35943421|doi=10.1080/15563650.2022.2101469|first5=L.|last5=Keating|first6=R.|last6=Macfarlane|first7=F.|last7=Cantle|first8=S.|last8=Hudson|first9=S. H. L.|last9=Thomas}}</ref> It is a similarly potent CB<sub>1</sub> agonist, with an EC<sub>50</sub> of 6.36 nM.<ref>{{cite journal | vauthors = Cannaert A, Sparkes E, Pike E, Luo JL, Fang A, Kevin RC, Ellison R, Gerona R, Banister SD, Stove CP | display-authors = 6 | title = Synthesis and ''in Vitro'' Cannabinoid Receptor 1 Activity of Recently Detected Synthetic Cannabinoids 4F-MDMB-BICA, 5F-MPP-PICA, MMB-4en-PICA, CUMYL-CBMICA, ADB-BINACA, APP-BINACA, 4F-MDMB-BINACA, MDMB-4en-PINACA, A-CHMINACA, 5F-AB-P7AICA, 5F-MDMB-P7AICA, and 5F-AP7AICA | journal = ACS Chemical Neuroscience | volume = 11 | issue = 24 | pages = 4434–4446 | date = December 2020 | pmid = 33253529 | doi = 10.1021/acschemneuro.0c00644 | s2cid = 227246346 }}</ref><ref>{{cite journal | vauthors = Pike E, Grafinger KE, Cannaert A, Ametovski A, Luo JL, Sparkes E, Cairns EA, Ellison R, Gerona R, Stove CP, Auwärter V, Banister SD | display-authors = 6 | title = Systematic evaluation of a panel of 30 synthetic cannabinoid receptor agonists structurally related to MMB-4en-PICA, MDMB-4en-PINACA, ADB-4en-PINACA, and MMB-4CN-BUTINACA using a combination of binding and different CB<sub>1</sub> receptor activation assays: Part I-Synthesis, analytical characterization, and binding affinity for human CB<sub>1</sub> receptors | journal = Drug Testing and Analysis | volume = 13 | issue = 7 | pages = 1383–1401 | date = July 2021 | pmid = 33787091 | doi = 10.1002/dta.3037 }}</ref>


== See also ==
== See also ==

Revision as of 21:24, 10 August 2022

ADB-BINACA
Legal status
Legal status
Identifiers
  • N-[(2S)-1-amino-3,3-dimethyl-1-oxobutan-2-yl]-1-benzyl-1H-indazole-3-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H24N4O2
Molar mass364.449 g·mol−1
3D model (JSmol)
  • O=C(NC(C(N)=O)C(C)(C)C)C1=NN(CC2=CC=CC=C2)C3=C1C=CC=C3
  • InChI=1S/C21H24N4O2/c1-21(2,3)18(19(22)26)23-20(27)17-15-11-7-8-12-16(15)25(24-17)13-14-9-5-4-6-10-14/h4-12,18H,13H2,1-3H3,(H2,22,26)(H,23,27)
  • Key:IUFIUAWRCUVUCQ-UHFFFAOYSA-N

ADB-BINACA is a cannabinoid designer drug that has been found as an ingredient in some synthetic cannabis products.[1] It was originally developed by Pfizer as a potential analgesic, and is a potent agonist of the CB1 receptor with a binding affinity (Ki) of 0.33 nM and an EC50 of 14.7 nM.[2]

ADB-BUTINACA

ADB-BUTINACA
Legal status
Legal status
Identifiers
  • N-[(2S)-1-amino-3,3-dimethyl-1-oxobutan-2-yl]-1-butyl-1H-indazole-3-carboxamide
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H26N4O2
Molar mass330.432 g·mol−1
3D model (JSmol)
  • O=C(N[C@H](C(N)=O)C(C)(C)C)C1=NN(CCCC)C2=C1C=CC=C2
  • InChI=1S/C18H26N4O2/c1-5-6-11-22-13-10-8-7-9-12(13)14(21-22)17(24)20-15(16(19)23)18(2,3)4/h7-10,15H,5-6,11H2,1-4H3,(H2,19,23)(H,20,24)/t15-/m1/s1
  • Key:GPWADXHYJAZPAX-OAHLLOKOSA-N

The analogue with a 1-butyl substitution on the indazole ring rather than 1-benzyl has also been sold as a designer drug under the name ADB-BINACA, but is now more commonly referred to as ADB-BUTINACA to avoid confusion with the benzyl compound.[3][4][5][6][7] It is a similarly potent CB1 agonist, with an EC50 of 6.36 nM.[8][9]

See also

References

  1. ^ Qian Z, Hua Z, Liu C, Jia W (2016). "Four types of cannabimimetic indazole and indole derivatives, ADB-BINACA, AB-FUBICA, ADB-FUBICA, and AB-BICA, identified as new psychoactive substances". Forensic Toxicology. 34: 133–143. doi:10.1007/s11419-015-0297-2. PMC 4705129. PMID 26793280.
  2. ^ WO 2009106982, "Indazole Derivatives" 
  3. ^ Kavanagh P, Pechnikov A, Nikolaev I, Dowling G, Kolosova M, Grigoryev A (August 2021). "Detection of ADB-BUTINACA Metabolites in Human Urine, Blood, Kidney and Liver". Journal of Analytical Toxicology. doi:10.1093/jat/bkab088. PMID 34341821.
  4. ^ Sia CH, Wang Z, Goh EM, Tan YL, Fong CY, Moy HY, Chan EC (November 2021). "Urinary Metabolite Biomarkers for the Detection of Synthetic Cannabinoid ADB-BUTINACA Abuse". Clinical Chemistry. 67 (11): 1534–1544. doi:10.1093/clinchem/hvab134. PMID 34387654.
  5. ^ Kronstrand R, Norman C, Vikingsson S, Biemans A, Valencia Crespo B, Edwards D, et al. (November 2021). "The metabolism of the synthetic cannabinoids ADB-BUTINACA and ADB-4en-PINACA and their detection in forensic toxicology casework and infused papers seized in prisons". Drug Testing and Analysis. doi:10.1002/dta.3203. PMID 34811926. S2CID 244490343.
  6. ^ Wang, Yue; Pan, Yefei; Yang, Hongkun; Liu, Jinlei; Wurita, Amin; Hasegawa, Koutaro (2022). "Quantification of MDMB-4en-PINACA and ADB-BUTINACA in human hair by gas chromatography–tandem mass spectrometry". Forensic Toxicology. doi:10.1007/s11419-022-00615-z. ISSN 1860-8973.
  7. ^ King, A.; Hill, S. L.; Pucci, M.; Bailey, G.; Keating, L.; Macfarlane, R.; Cantle, F.; Hudson, S.; Thomas, S. H. L. (August 2022). "Clinical features associated with ADB-BUTINACA exposure in patients attending emergency departments in England". Clinical Toxicology: 1–5. doi:10.1080/15563650.2022.2101469. ISSN 1556-3650. PMID 35943421.
  8. ^ Cannaert A, Sparkes E, Pike E, Luo JL, Fang A, Kevin RC, et al. (December 2020). "Synthesis and in Vitro Cannabinoid Receptor 1 Activity of Recently Detected Synthetic Cannabinoids 4F-MDMB-BICA, 5F-MPP-PICA, MMB-4en-PICA, CUMYL-CBMICA, ADB-BINACA, APP-BINACA, 4F-MDMB-BINACA, MDMB-4en-PINACA, A-CHMINACA, 5F-AB-P7AICA, 5F-MDMB-P7AICA, and 5F-AP7AICA". ACS Chemical Neuroscience. 11 (24): 4434–4446. doi:10.1021/acschemneuro.0c00644. PMID 33253529. S2CID 227246346.
  9. ^ Pike E, Grafinger KE, Cannaert A, Ametovski A, Luo JL, Sparkes E, et al. (July 2021). "Systematic evaluation of a panel of 30 synthetic cannabinoid receptor agonists structurally related to MMB-4en-PICA, MDMB-4en-PINACA, ADB-4en-PINACA, and MMB-4CN-BUTINACA using a combination of binding and different CB1 receptor activation assays: Part I-Synthesis, analytical characterization, and binding affinity for human CB1 receptors". Drug Testing and Analysis. 13 (7): 1383–1401. doi:10.1002/dta.3037. PMID 33787091.
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